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Last October, executives from one of Bernard Madoff’s key money sources, Fairfield Greenwich Group, asked for a meeting with the obsessively secretive man who, just two months later, would confess to running the biggest swindle of all time.

Fairfield Greenwich’s clients were asking pointed questions about Madoff - about his strategy, trades, and the safety of their money. The inquiries were driven in part by the turmoil in the markets: Lehman Brothers had just failed, and the stock market was plummeting amid the global credit crisis.

But during the Oct. 2 meeting at his Manhattan office, Madoff refused to provide the Fairfield Greenwich executives with the answers they sought, even basics like the names of traders working on Fairfield’s account. This, despite the New York hedge fund’s 18-year history with Madoff, and the $7 billion of client funds it had entrusted to him.

This is one of many red flags Massachusetts Secretary of State William F. Galvin said should have alerted Fairfield Greenwich that Madoff was hiding something, according to a prehearing memorandum filed earlier this month by Galvin’s securities division. The state sued Fairfield for fraud in April, contending that its executives failed to conduct adequate oversight of Madoff’s operation, while assuring clients otherwise, and taking more than $300 million in fees in the past three years alone.

Galvin’s office is preparing for hearings sched uled to begin Sept. 9, at which regulators will question 23 people under oath, including Fairfield founder Walter Noel and other employees. They also will hear testimony from some of the firm’s Massachusetts investors, among them Charles O. Wood III and Miriam M. Wood, Boston philanthropists who are benefactors of the Harvard Art Museum.

A spokesman for Fairfield Greenwich, Seth Faison, said, “No one at Fairfield Greenwich had any inkling that anything was amiss with Madoff before Dec. 11, 2008.’’ He said the prehearing memorandum is inaccurate and that many of its assertions are “flat-out wrong,’’ without citing specifics.

An attorney for Noel said he denies the charges against the firm.

If the market’s collapse was Madoff’s undoing - the event that would unravel his scheme and land him in prison for 150 years - it was also the first time Madoff customers of many stripes asked questions about the double-digit returns they reaped with him for years.

The Massachusetts memo portrays Fairfield Greenwich as growing more aware over the course of 2008 of gaps in its knowledge of Madoff’s operations. Executives acknowledged to state regulators and to each other in internal e-mails that they couldn’t answer the increasingly probing questions of some clients. They didn’t know Madoff’s trading strategy, they knew only a handful of Madoff’s employees, and had never been allowed to see the trading floor where Madoff was allegedly buying and selling securities for their customers.

Instead of disclosing their concerns to nervous clients, Fairfield Greenwich executives assured them they were conducting rigorous oversight and that all was well, according to the state’s memo.

Galvin, in an interview, called the relationship between Fairfield and Madoff “incestuous,’’ and said, “We have a strong case based on the repeated failure of Fairfield Greenwich to do due diligence.’’

Lawyers for some of Fairfield’s principals insist the firm had no idea Madoff’s activities were suspect. Chief risk officer Amit Vijayvergiya routinely analyzed thousands of trade reports that Madoff sent him, said his lawyer, Mark Goodman, and asked Madoff probing questions whenever he spoke to him.

“Amit Vijayvergiya had absolutely no concern at all that there was anything amiss or anything wrong with respect to Bernie Madoff,’’ his lawyer said.

Yet back in 2005, when inspectors at the Securities and Exchange Commission were conducting an examination of Madoff, following a tip by whistle-blower Harry Markopolos, Madoff coached Fairfield executives on what to say to the regulators, according to Galvin’s complaint. He prefaced his instructions with the remark, “Obviously, first of all, this conversation never took place,’’ according to a transcript of the conversation cited by Galvin’s office.

Fairfield Greenwich has said its executives told the truth to the SEC in 2005. The SEC has said the probe did not turn up any wrongdoing.

By last year, Fairfield was feeling far more pressure. In May 2008, a large European investment client, Unigestion, asked if Madoff really made the trades he claimed, the state said. Dissatisfied with Fairfield’s assurances, Unigestion withdrew $75 million by August.

In one e-mail to his colleagues on Aug. 20, 2008, Vijayvergiya said he had reassured a customer that after two decades of dealing with Madoff’s firm, “we have good knowledge of BLM’s business,’’ according to text of the e-mail cited in Galvin’s memo.

Yet just the day before, Vijayvergiya wrote in another internal e-mail that “unfortunately there are certain aspects of BLM’s operations that remain unclear and although we are attempting to obtain responses from Bernie Madoff . . . this process could take some time.’’

After the Unigestion withdrawal, Fairfield executives requested a meeting with Madoff. They had so many questions, according to the state’s memorandum, that the executives decided to ask Madoff only the most important ones.

Fairfield sent Madoff a list of questions in advance of the Oct. 2 meeting, asking for a list of key people involved in trading and a description of their roles. Madoff’s written response said the employees were “traders, systems, analysts, programmers and operations people. No names given.’’ Fairfield executives weren’t able to glean more specifics during the meeting.

That same month, another big customer, JPMorgan, asked about the trading counterparties in Madoff’s options-investment strategy; when Fairfield couldn’t answer, the Wall Street giant withdrew its money.

Though they could not answer clients’ specific questions, Fairfield Greenwich executives drummed up a stock reply to respond to them. According to the memorandum, a Nov. 14 e-mail by a Fairfield analyst laid out a “standard response’’ for clients, “setting forth the basis on which Fairfield was satisfied that adequate controls existed to ensure that the Madoff assets were properly supervised.’’